Moving from Insider to Outsider: Derek Webb’s Peaceful Disruption

Isn’t it fun to be part of the in-crowd? Where you can connect with people who are of like minds and spirits, where everyone seems to be headed in the same direction? But what if you start having nagging questions as an insider that don’t seem to get resolved, and even worse, are met with disdain or fear from other members of your group? This can be a scary place for so many of us. For the purposes of our conversation today–we’re talking about when it happens in religious spaces. For years, singer/songwriter Derek Webb was very much on the “inside” of what was happening in Christendom as a top selling, award winning Christian artist, songwriter and worship leader. It took a few disruptions to his own life that sent him down the road to evaluating his faith, his beliefs and how he wanted to move forward with the new information he’d gained. Now, decidedly an “outsider” who tries to still take up space in the Christian zeitgeist to potentially model a different way of living, Derek has gone on to record solo albums and also work with artists that aren’t typical to Christian music–like drag queen Flamy Grant—with whom, incidentally, he attended the Gospel Music Dove Awards in 2023 (and who also had a number one Christian song pop up on the charts), with the intention of making people who are Christian and LGBTQ+IA feel less alone. In this episode, Jen and Derek compare their journeys as “peaceful disruptors,” what it cost them and what they gained in the process

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Thought-Provoking Quotes:

“So now here I am, 20 years [after going solo] and I'm spoiled into thinking that I can write songs about things no one else is writing songs about, and that's kind of my thing now.” - Derek Webb

“I'd been so obsessed on thinking about, obsessed on my language about God, that I forgot to apply it to the way I behave in the world, the way I treat other people, which is ethics. And I realized, 'Oh no, how did I miss that?' As I stand before you as the ringing symbol, the clanging gong when I've got all the right words and none of the love, none of the fruit.” - Derek Webb

“I had to rebuild at almost 40, I had to rebuild a whole life and reckon with the fallout, at least my part of the responsibility of some real hurt. I caused a lot of people who I love to hurt, the people I love more than anybody in the world. And it humbled me.” - Derek Webb

“Flamy Grant and Semler were not the first two queer artists to have number-one albums and singles on the Christian music charts. It has happened so many times over the years, but by people who are closeted and people who live in tremendous fear in that space because they know they will be immediately rejected, excluded, marginalized, out.” - Derek Webb

Resources Mentioned in This Episode:

Caedmon’s Call

Aaron Tate’s Website

Second Baptist Church

She Must and Shall Go Free - Album by Derek Webb

Essential Records

Third Day

Jars Of Clay

Plumb

The Prayer of Jabez

Wedding Dress by Derek Webb

Grace Point Church

The Jesus Hypothesis

Boys Will Be Girls Music Video ...